Compounds which have activity at M1 receptor and their uses in medicine

Abstract

Compounds of the general formula And their use in the treatment of psychotic disorders and cognitive impairment are disclosed.

1 . A compound which is:
 6-Methyl-1-[1-(cis-4-methoxycyclohexyl)-4-piperidinyl]-1,3-dihydro-2H-benzimidazol-2-one;   6-Methyl-1-[1-(trans-4-methoxycyclohexyl)-4-piperidinyl]-1,3-dihydro-2H-benzimidazol-2-one;   1-{1-[trans-4-(Ethyloxy)cyclohexyl]-4-piperidinyl}-6-methyl-1,3-dihydro-2H-benzimidazol-2-one;   1-{1-[cis-4-(Ethyloxy)cyclohexyl]-4-piperidinyl}-6-methyl-1,3-dihydro-2H-benzimidazol-2-one;   6-Methyl-1-{1-[cis-4-(propyloxy)cyclohexyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one;   6-Methyl-1-{1-[trans-4-(propyloxy)cyclohexyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one;   6-Methyl-1-(1-{trans-4-[(1-methylethyl)oxy]cyclohexyl}-4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one;   6-Methyl-1-{1-[cis-1-methyl-4-(methyloxy)cyclohexyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one;   6-Methyl-1-{1-[trans-1-methyl-4-(methyloxy)cyclohexyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one;   6-Methyl-1-(1-{cis-4-[(1-methylethyl)oxy]cyclohexyl}-4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one;   cis-(1-[4-(Ethoxyl)cyclohexyl]-4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one;   trans 1-(1-[4-(Ethoxyl)cyclohexyl]-4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one;   1-{1-[trans-4-(Ethyloxy)cyclohexyl]-4-piperidinyl}-6-fluoro-1,3-dihydro-2H-benzimidazol-2-one;   6-Bromo-1-{1-[trans-4-(ethyloxy)cyclohexyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one;   1-{1-[cis-4-(Ethyloxy)cyclohexyl]-4-piperidinyl}-6-(trifluoromethyl)-1,3-dihydro-2H-benzimidazol-2-one;   6-Ethyl-1-{1-[trans-4-(ethyloxy)cyclohexyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one;   6-Cyclopropyl-1-{1-[trans-4-(ethyloxy)cyclohexyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one;   1-{1-[trans-4-(Ethyloxy)cyclohexyl]-4-piperidinyl}-6-(methyloxy)-1,3-dihydro-2H-benzimidazol-2-one;   cis-1-{1-[4-(Ethoxy)cyclohexyl]-4-piperidinyl}-6-[(trifluoromethyl)oxy]-1,3-dihydro-2H-benzimidazol-2-one;   trans-1-{1-[4-(Ethoxy)cyclohexyl]-4-piperidinyl}-6-[(trifluoromethyl)oxy]-1,3-dihydro-2H-benzimidazol-2-one;   6-Methyl-1-[1-(4-trifluoromethoxycyclohexyl)-4-piperidinyl]-1,3-dihydro-2H-benzimidazol-2-one;   1-(1-{cis-4-[(Cyclopropylmethyl)oxy]cyclohexyl}-4-piperidinyl)-6-methyl-1,3-dihydro-2H-benzimidazol-2-one;   1-(1-{trans-4-[(Cyclopropylmethyl)oxy]cyclohexyl}-4-piperidinyl)-6-methyl-1,3-dihydro-2H-benzimidazol-2-one;   trans-6-Methyl-1-[1-(4-cyclopropyloxycyclohexyl)-4-piperidinyl]-1,3-dihydro-2H-benzimidazol-2-one;   cis-1-(1-[4-(Propyloxy)cyclohexyl]-4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one;   trans-1-(1-[4-(Propyloxy)cyclohexyl]-4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one;   6-Bromo-1-{1-[trans-4-(propyloxy)cyclohexyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one;   6-Ethyl-1-{1-[trans-4-(propyloxy)cyclohexyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one;   6-Cyclopropyl-1-{1-[trans-4-(propyloxy)cyclohexyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one;   cis-1-{1-[4-(Propyloxy)cyclohexyl]-4-piperidinyl}-6-[(trifluoromethyl)oxy]-1,3-dihydro-2H-benzimidazol-2-one;   trans-1-{1-[4-(Propyloxy)cyclohexyl]-4-piperidinyl}-6-[(trifluoromethyl)oxy]-1,3-dihydro-2H-benzimidazol-2-one;   1-{1-[cis-4-(Ethyloxy)-1-methylcyclohexyl]-4-piperidinyl}-6-methyl-1,3-dihydro-2H-benzimidazol-2-one;   1-{1-[trans-4-(ethyloxy)-1-methylcyclohexyl]-4-piperidinyl}-6-methyl-1,3-dihydro-2H-benzimidazol-2-one;   6-Methyl-1-{1-[cis-1-methyl-4-(propyloxy)cyclohexyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one;   6-Methyl-1-{1-[trans-1-methyl-4-(propyloxy)cyclohexyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one;   trans-6-Methyl-1-[1-(1-ethyl-4-propoxycyclohexyl)-4-piperidinyl]-1,3-dihydro-2H-benzimidazol-2-one;   3-{1-[trans-4-(Ethyloxy)cyclohexyl]-4-piperidinyl}-2-oxo-2,3-dihydro-1H-benzimidazole-5-carbonitrile;   3-{1-[trans-4-(Ethyloxy)-1-methylcyclohexyl]-4-piperidinyl}-2-oxo-2,3-dihydro-1H-benzimidazole-5-carbonitrile;   1-{1-[trans-4-(Ethyloxy)cyclohexyl]-4-piperidinyl}-6-(methylsulfonyl)-1,3-dihydro-2H-benzimidazol-2-one;   6-Methyl-1-{1-[cis-4-(2-propyn-1-yloxy)cyclohexyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one;   6-Methyl-1-{1-[trans-4-(2-propyn-1-yloxy)cyclohexyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one;   1-{1-[trans-4-(Ethyloxy)-1-methylcyclohexyl]-4-piperidinyl}-6-fluoro-1,3-dihydro-2H-benzimidazol-2-one;   6-Fluoro-1-{1-[trans-1-methyl-4-(methyloxy)cyclohexyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one;   6-Chloro-1-{1-[trans-1-methyl-4-(methyloxy)cyclohexyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one;   6-(Ethyloxy)-1-{1-[trans-1-methyl-4-(methyloxy)cyclohexyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one;   6-(Ethyloxy)-1-{1-[trans-4-(ethyloxy)-1-methylcyclohexyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one;   6-Chloro-1-{1-[trans-4-(ethyloxy)-1-methylcyclohexyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one;   
       or a salt thereof. 
     
     
         2 . A pharmaceutical composition comprising a compound claimed in  claim 1  and a pharmaceutically acceptable carrier. 
     
     
         3 . A method of treating a psychotic disorder or cognitive impairment, which comprises administering to a mammal in need thereof an effective amount of a compound of  claim 1 .